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They absolutely can end up together as both Johnson and Winslow have Kentucky on their final list of schools. Winslow is ultra competitive and brings a lot to the table and influences the outcome of a contest in many ways. On the fast break he is a good facilitator and decision-maker, as well as an excellent finisher.
Put him in the halfcourt set and he gladly takes on the challenge to defend the other team's best player. He is the best in the class at individual defense and can defend multiple positions.
Offensively, Winslow will penetrate and find his open teammates as his vision and unselfishness are evident. His jumper is solid from the elbow and he certainly effects the game without scoring , but he is not wired nor does he possess all the true skills needed to be a difference-maker as a point guard. He can fill in for a short time as a point guard in a pinch as he does process the game well.
If the Wildcats of Kentucky were fortunate to land both they would still need a true point guard to lead their team.